Ammonium Chloride → N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

HRID 399351Notes

Reaction equation

HRID 399351 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH2:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH2:33])=[N:24]2)C=CC=CC=1.C(=O)=O.CC(C)=O.Br[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[C:55]2[N:59]([C:60]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=3)([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[N:58]=[N:57][N:56]=2)=[CH:45][CH:44]=1.[Cl-].[NH4+]>C(OCC)(=O)C.CCCCCC.C1COCC1.CN1CCCN(C)C1=O>[C:9]1([CH2:21][CH2:22][N:23]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25]([NH:33][CH2:42][C:43]3[CH:44]=[CH:45][C:46]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=4[C:55]4[N:59]([C:60]([C:73]5[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=5)([C:67]5[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=5)[C:61]5[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=5)[N:58]=[N:57][N:56]=4)=[CH:47][CH:48]=3)=[N:24]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 18522661Acetone cardice2×HCID 221038291-(2-Phenylethyl)-3-amino-4-ethoxycarbonylpyrazoleHCID 86604122LDA cyclohexane

Product 1

HCID 67637880N-[1-(2-phenylethyl)-4-ethoxycarbonylpyrazol-3-yl]-N-[(2'-(N-triphenylmethyl-(1H-tetrazol-5-yl))biphenyl-4-yl) methyl]amine

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

2.1 ml of 1.5M lithium diisopropylamide/cyclohexane solution were added to THF solution (35 ml) containing 363 mg of 1-(2-phenylethyl)-3-amino-4-ethoxycarbonylpyrazole and 0.40 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, while cooling with dry ice-acetone, and stirred at room temperature for 15 minutes. The mixture was again cooled with dry ice-acetone, and 10 ml of THF solution of 877 mg of 4-bromomethyl-2'-[N-triphenylmethyl-(1H-tetrazol-5-yl)]biphenyl were added thereto and stirred at room temperature for 5.5 hours. 10 ml of aqueous ammonium chloride solution was added to the reaction solution, THF was distilled off under reduced pressure, and the resultant was extracted with 50 ml of dichloromethane. The resulting extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (n-hexane--ethyl acetate=3:1→2:1) to obtain 234 mg of the intended compound as a pale yellow, amorphous solid.

Workup

  1. additionwere added
  2. stirringstirred at room temperature for 5.5 hours
  3. distillationwas distilled off under reduced pressure
  4. extractionthe resultant was extracted with 50 ml of dichloromethane
  5. extractionThe resulting extract
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained

Sources & evidence

ORD record
ord-bb78c4534fb74fd196d94db81d4ecb28
Source dataset
uspto-grants-1998_10
Patent number
US05817828

Reaction notes

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